4295-28-7Relevant academic research and scientific papers
One-pot Graebe-Ullmann synthesis of γ-carbolines under microwave irradiation
Molina, Andres,Vaquero, Juan J.,Garcia-Navio, Jose L.,Alvarez-Builla, Julio
, p. 2673 - 2676 (1993)
One-pot efficient and simple synthesis of γ-carboline derivatives by the Graebe-Ullmann method was conducted in a commercial microwave oven in a few minutes at a low energy level and using erlenmeyer as adequate reaction vessels. Yields are similar to those obtained by conventional heating.
Novel convenient one-pot method for the synthesis of indoloquinolines
Aksenov,Gasanova,Abakarov,Aksenova,Aksenov
, p. 836 - 840 (2019/06/03)
A novel one-pot method based on the sequence of the Fisher reaction between nitroacetophenone and phenylhydrazines, the reduction with metallic tin directly in polyphosphoric acid, and acylation has been developed for the synthesis of indoloquinolines. Th
A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
Aksenov, Nicolai A.,Aksenov, Alexander V.,Kornienko, Alexander,De Carvalho, Annelise,Mathieu, Véronique,Aksenov, Dmitrii A.,Ovcharov, Sergei N.,Griaznov, Georgii D.,Rubin, Michael
, p. 36980 - 36986 (2018/11/23)
A second generation polyphosphoric acid-mediated one-pot three-component synthesis of indoloquinoline scaffold is developed. This improved version of the process involves electrophilically activated nitroalkanes for the installation of strategic C-C and C-N bonds and ring C assembly. This modification allows the elimination of unnecessary solvent change operations and all steps are carried out in a true, uninterrupted one-pot manner. A further improvement involves the possibility to install an ortho-amino group in situ. A synthetic application of this method is showcased by the concise synthesis of an isocryptolepine alkaloid and its synthetic analogs with potent anticancer activities.
One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of Isocryptolepine
Aksenov, Alexander V.,Aksenov, Dmitrii A.,Orazova, Naila A.,Aksenov, Nicolai A.,Griaznov, Georgii D.,De Carvalho, Annelise,Kiss, Robert,Mathieu, Véronique,Kornienko, Alexander,Rubin, Michael
, p. 3011 - 3018 (2017/03/23)
Indolo[3,2-c]quinolones have been efficiently synthesized via an acid-mediated, one-pot, three-component condensation of arylhydrazines, o-aminoacetophenones, and triazines or nitriles. The synthetic application of this method is showcased by the concise synthesis of isocryptolepine alkaloid and a series of its synthetic analogues with demonstrated cancer cell antiproliferative activities.
Indole [3,2-c] quinoline compound or its pharmaceutically acceptable salts and its preparation method and application
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Paragraph 0036; 0044-0047, (2016/10/10)
The invention discloses indole[3,2-c]quinoline compounds represented by formula I or pharmaceutically acceptable salts thereof, and a preparation method and an application thereof, and belongs to the technical field of the pharmaceutical chemistry. The in
An alternative one-pot gold-catalyzed approach to the assembly of 11H-indolo[3,2-c]quinolines
Abbiati, Giorgio,Arcadi, Antonio,Chiarini, Marco,Marinelli, Fabio,Pietropaolo, Emanuela,Rossi, Elisabetta
, p. 7801 - 7808 (2013/04/23)
A new one-pot approach was developed to construct the 11H-indolo[3,2-c] quinoline scaffold through a gold-catalysed reaction of 2-[(2-aminophenyl) ethynyl]phenylamine derivatives with aldehydes. The broad scope and the high regioselectivity of this new pr
Facile assembly of 11 H -indolo[3,2-c]quinoline by a two-step protocol involving a regioselective 6- endo -cyclization promoted by the hendrickson reagent
Xu, Min,Hou, Qiwen,Wang, Shaozhong,Wang, Huaqin,Yao, Zhu-Jun
, p. 626 - 634 (2011/04/15)
An expedient approach was developed to construct the 11H-indolo[3,2-c] quinoline scaffold starting from acyclic alkyne substrates. The five- and six-membered nitrogen-containing rings in the tetracyclic skeleton were elaborated efficiently by gold(III)-ca
Convenient and efficient microwave-assisted synthesis of a methyl derivative of the fused indoloquinoline alkaloid cryptosanguinolentine
Gengan, Robert M.,Pandian, Pitchai,Kumarsamy, Chandraprakash,Mohan, Palathurai S.
experimental part, p. 3171 - 3178 (2010/09/04)
An efficient synthesis of a methyl derivative of the indoloquinoline alkaloid cryptosanguinolentine based on microwave-assisted reactions is described. The microwave-assisted synthesis of an intermediate 4-hydroxy-2-methylquinoline yielded 86% of the desired product and other intermediates prepared yielded high % of products in shorter reaction times, under optimum conditions, as compared to traditional methods.
Photo induced synthesis of methyl derivative of cryptosanguinolentine
Pitchai,Mohan,Gengan
experimental part, p. 692 - 696 (2009/12/24)
A simpler method to synthesize methyl derivative of an alkaloid ciyprosanguinolentine is described. 4-Hydroxy-2- methylquinoline is iodized using iodine, potassium iodide and aqueous sodium hydroxide and dehydroxyhalogenated with phosphorous oxychloride. The respective anilinoquinoline is prepared and cyclized by UV irradiation. Upon selective methylation 5,6-dimethyl-5//-indolo[3,2-c]quinoline is produced which is utilized as a DNA intercalating agent.
Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives
Dhanabal,Sangeetha,Mohan
, p. 6258 - 6263 (2007/10/03)
A three-step synthesis of indoloquinoline alkaloids is described. The reaction of 2,3 and 4-substituted haloquinolines with anilines afforded the respective anilinoquinolines, which upon photocyclization gave the indoloquinolines. By regioselective methylation on quinoline nitrogen, furnished the alkaloids cryptotackieine, cryptosanguinolentine, cryptolepine, and the synthetic isomer isoneocryptolepine. Their methyl derivatives were also synthesized in search of new antiplasmodial drugs and DNA intercalating agents.
